Cyanoacetic acid → 2-cyano-3-[5-(9,9-dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]acrylic acid

HRID 1965876Notes

Reaction equation

HRID 1965876 reaction equation
[CH2:1]([C:5]1([CH2:34][CH2:35][CH2:36][CH3:37])[C:17]2[CH:16]=[C:15]([C:18]3[S:22][C:21]([CH:23]=O)=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([N:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].[C:38]([CH2:40][C:41]([OH:43])=[O:42])#[N:39]>C(#N)C.N1CCCCC1>[C:38]([C:40](=[CH:23][C:21]1[S:22][C:18]([C:15]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([N:25]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:9][CH:10]=4)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:34][CH2:35][CH2:36][CH3:37])[C:17]=3[CH:16]=2)=[CH:19][CH:20]=1)[C:41]([OH:43])=[O:42])#[N:39]

Participants

5

Reactant 2

HCID 9740Cyanoacetic acidHCID 86641779HCID 86641779, compound

Product 1

HCID 667622752-cyano-3-[5-(9,9-dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]acrylic acid

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6342AcetonitrileSolvent

Procedure

As shown in Scheme 2, 7-bromo-9H-fluoren-2-ylamine is reacted with 1-iodobutane to form (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21). Then, (7-bromo-9,9-dibutyl-9H-fluoren-2-yl)-dibutylamine (21) is reacted with 5-formyl-2-thiopheneboronic acid by Suzuki coupling reaction to obtain 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a). Finally, in acetonitrile, 5-(9,9-Dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (22a) is reacted with cyanoacetic acid by using piperidine as a catalyst, to obtain 2-Cyano-3-[5-(9,9-dibutyl-7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]-acrylic acid (23a).

Sources & evidence

ORD record
ord-d7963c918ee14bd2875a138daec0cefd
Source dataset
uspto-grants-2013_04
Patent number
US08419808B2

Reaction notes

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